Sulfamic Acid → 4-Phenylthiophene-2-carboxylic acid

HRID 1177968Notes

Reaction equation

HRID 1177968 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[O:13])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)([OH:16])N.Cl([O-])=O.[Na+]>CC(C)=O.O.O>[C:1]1([C:7]2[CH:8]=[C:9]([C:12]([OH:16])=[O:13])[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 50094674-Phenylthiophene-2-carbaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 12231844-Phenylthiophene-2-carboxylic acidYield 62.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

4-phenyl-thiophene-2-carboxaldehyde (150 mg, 0.80 mmol) was dissolved in acetone-water mixture (2:1) (3 mL) and cooled to 0° C. To this reaction mixture was added sulphamic acid (232 mg, 2.38 mmol) and sodium chlorite (288 mg, 3.18 mmol) dissolved in minimum amount of water. The resulting reaction mixture was allowed to stir at room temperature for half an hour. The reaction mixture was then diluted with water and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over sodium sulphate and concentrated to afford 100 mg (62.5% yield) of 4-Phenyl-thiophene-2-carboxylic acid.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-483b7c4a0e274a36941c47fa0a62c691
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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